36939-28-3

Basic information

• Product Name: 1-methyl-2-phenylpiperidine
• Synonyms: 1-methyl-2-phenylpiperidine;(2R)-1-Methyl-2β-phenylpiperidine;N-Methyl-2-phenyl-D2-tetrahydropyridine
• CAS NO: 36939-28-3
• Molecular Formula: C₁₂H₁₇N
• Molecular Weight: 175.27008
• EINECS: 253-282-4
• Mol File: 36939-28-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 247°Cat760mmHg
• Flash Point: 94.2°C
• Appearance: /
• Density: 0.964g/cm³
• Vapor Pressure: 0.0263mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: 1-methyl-2-phenylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-2-phenylpiperidine(36939-28-3)
• EPA Substance Registry System: 1-methyl-2-phenylpiperidine(36939-28-3)

Safety Data

• Hazardous Substances Data: 36939-28-3(Hazardous Substances Data)

Usage

General Description

1-methyl-2-phenylpiperidine, also known as MPPP, is a chemical compound that belongs to the class of piperidine derivatives. It is a psychoactive central nervous system stimulant and is also known as a designer drug. MPPP is synthesized from a precursor chemical called 1-methyl-4-phenyl-4-propionoxypiperidine (MPTP), which is converted into MPPP through a chemical reaction. MPPP has been found to have stimulant and hallucinogenic effects, and has been abused for its psychoactive properties. However, it is also known to have serious side effects, including neurotoxicity and potential for addiction. Due to its potency and adverse effects, MPPP is now a controlled substance in many countries, and its use is restricted for medical and research purposes only.

InChI:InChI=1/C12H17N/c1-13-10-6-5-9-12(13)11-7-3-2-4-8-11/h2-4,7-8,12H,5-6,9-10H2,1H3

Upstream product

• 122333-70-4 cis-N-Methyl-5-phenyl-4-penten-1-amine 
• 1008-89-5 2-phenylpyridine 
• 124-38-9 carbon dioxide 
• 28525-69-1 (4E)-5-phenyl-4-pentenoic acid 
• 122333-64-6 trans-N-Methyl-5-phenyl-4-penten-1-amine 
• 131529-91-4 (E)-5-Phenyl-pent-4-enoic acid methylamide 
• 63082-55-3 diethyl (E)-cinnamyl malonate 
• 22768-07-6 (E)-ethyl 5-phenylpent-4-enoate 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 100-46-9 benzylamine 
• 104936-74-5 N-Benzyl-N'-tert-butyl-N-methyl-formamidine 
• 6343-54-0 N-benzylformamide 
• 17105-71-4 N-methyl-N-benzylformamide 
• 931-20-4 1-methylpiperidin-2-one 

Downstream Products

• 122333-70-4 cis-N-Methyl-5-phenyl-4-penten-1-amine 
• 3358-68-7 2-Methyl-7-phenyl-hexahydro-1,2-oxazepin 

Relevant articles and documents

Catalytic methylation of C-H bonds using CO2 and H2

Formation of C-C bonds from CO2 is a much sought after reaction in organic synthesis. To date, other than C-H carboxylations using stoichiometric amounts of metals, base, or organometallic reagents, little is known about C-C bond formation. In fact, to the best of our knowledge no catalytic methylation of C-H bonds using CO2 and H2 has been reported. Described herein is the combination of CO2 and H2 for efficient methylation of carbon nucleophiles such as indoles, pyrroles, and electron-rich arenes. Comparison experiments which employ paraformaldehyde show similar reactivity for the CO2/H2 system. Capturing: Carbon dioxide in the presence of H2 is shown to be an efficient methylating reagent for carbon nucleophiles such as 2-substituted indoles, pyrroles, and electron-rich arenes. Experimental data support the formal capture of formaldehyde. acac=acetylacetonate, triphos=1,1,1-tris(diphenylphosphinomethyl)ethane.

Photophysical and photochemical behavior of intramolecular-styrene-amine exciplexes

The photophysical and photochemical behavior of a series of secondary and tertiary ω-(β-styryl)aminoalkanes with one to five methylenes separating the styryl and amino groups has been investigated and compared to the intermolecular reactions of 1-phenylpropene with secondary and tertiary amines. The tertiary styrylamines form fluorescent intramolecular exciplexes, but fail to undergo intramolecular addition reactions. Both the rate constant for exciplex formation and the stability of the exciplex are dependent upon the length of the polymethylene chain connecting the chromophores. The failure of the tertiary amine exciplexes to undergo intramolecular addition is attributed to an unfavorable exciplex geometry for α-C-H transfer to the styrene double bond. While the secondary styrylamines do not form fluorescent exciplexes, the dependence of the styrene singlet lifetime upon the polymethylene chain length is similar to that for the tertiary styrylamines. Intramolecular N-H addition to the styrene double bond results in the formation of two regioisomeric (α-phenyl and α-benzyl) cyclic amines of different ring size. The regioisomer of larger ring size is favored except in the case in which four methylenes separate the chromophores. The effects of polymethylene chain length, solvent polarity, temperature, and the bulk of the N-alkyl group upon product yields and ratios are discussed in terms of a mechanism involving singlet exciplex and biradical intermediates.

Intramolecular Photochemical Addition Reactions of ω-Styrylaminoalkanes

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